Transition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group

Pd- or Ni-catalyzed C–H arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on regioselectivity of the reaction. In addition, we have shown that the efficiency of the Suzuki–Miyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct C–H arylation. The exploration of the chemical potential of the nitro group and a putative reaction mechanism are discussed.